The proposed research involves development of a concise, novel, biomimetic route for a synthesis of the communesins, a class of molecules exhibiting strong biological activity against a number of tumor cell lines. The chemistry investigated essentially consists of three parts: 1) discovery and development of a methodology for stereoselective radical/enolate coupling, 2) use of this methodology and known chemistry to access complex intermediates, which 3) will be used to elucidate the biosynthesis of the communesins. It is anticipated that the new methodology developed in parts 1) and 3) will facilitate the construction of analogues of the communesins and lead to a more profound understanding of the exhibited biological activity. Additionally, the chemistry developed will be broadly applicable and provide new disconnections and more facile access to compounds of clinical and medicinal importance. PUBLIC HEALTH RELEVANCE The proposed work aims at synthesis of compounds known to be toxic to a number of cancer cell lines. Chemistry developed in pursuit of the compounds is anticipated to allow efficient access to other targets of medicinal interest.